Why Trailwerks Even Exists

Hi 👋 My name is Maverick, and I built TrailWerks.

Something people often ask me is, "why?" That is kind of a complicated question, but I am putting pen to paper (or rather fingers to the keyboard) to approach the question from a few different angles and paint the picture of everything that built up to this very moment.

Maybe more people would see this if I made it as short form video content with catchy music, 3 second smash cuts, and more dancing, but I digress.

The story of Trailwerks really begins with the story of The Hiking Group. I spend a lot of time outdoors, and I was texting lots of friends to join me for the hikes. Sending the same messages over and over got exhausting. My marketing brain kicked in, and I thought... why not streamline the invite process. This could be a mailing list.

The Hiking Group has been through serveral technology and marketing stacks. At one point, The Hiking Group was a mailing list. At another point, The Hiking Group was a meetup group. As a software engineer, I felt certain that I could build something that bolsters a stronger group identity, costs less, and provides a better experience for both hikers and organizers than Meetup could, and I was right. I built a platform tailored for the hiking group that I started, and we affectionately call it "Boots."

I spent a couple of weeks building boots, and it was jam packed with features that made my life as an organizer much easier.

Truly, I built the best software for outdoor recreation organizers. I was grasping at straws for what else I could add to the paltform to make my life easier, but nothing came to mind.

I decided at that point to expand the platform so other outdoor recreation groups could white label and host their groups from the same software that I use to organize The Hiking Group, and that is where trailwerks entered the picture.

At the end of it, "boots" looks exactly the same, and our hikers noticed no difference, but now the Trailwerks platform powers The Hiking Group, and it is ready to power your outdoor recreation group, paddling club, climbing crew, scout troop, or well-organized-group-of-outdoorsy-friends in the same way.

In summary, I just like to hike, and I am a software engineer, and when you are a hammer then every problem is a nail, so Trailwerks just kind of made sense.

Tech is a means to facilitating in-person connection. Not an end in and of itself.

I am involved in a number of small groups and bible studies at church, and I have been organizing "The Hiking Group" for a little over 4 years now, and what I hear in each sphere is very consistent. People express loneliness, isolation, and a desire for community and connection. Strava stats confirm what I know anecdotally; clubs nearly 4X'd in 2025.

Outdoor group activities are an efficient and healthy container for in-person community. It is challenging to get lost in an endless feed of content while navigating the terrain of the trail, and folks bond over shared experiences like a challenging climb up a mountain, an unexpected rain shower during the hike, or seeing wildlife. Outdoor recreation is not just a niche. It is uniquely well suited to in-person connection.

Trailwerks is home-rolled. It came from a purpose built platform. From day 1, it was meant to facilitate the group that was using it. It was not born in a startup accelerator or boardroom.

The gap between development, event organizers, and hikers at Trailwerks is microscopic. Trailwerks was built by The Hiking Group eating our own dogfood. That is why I am confident that it will be just as useful for your outdoor recreation group!

And that is also why I am seeking early design partners at this stage. We want real outdoor recreation organizers who serve as stakeholders that shape the direction of the product, break assumptions that might have only worked for the hiking group, and keep the feedback loop tiny between user and product development.

You care deeply about the people who show up to your events week after week. The platform you host your group on (meetup, facebook) does not!

A user might visit your facebook group to learn about the latest events and then get stuck scrolling in a sea of addictive content, inflammatory news headlines, and advertisements. That is not what it looks like for your community to flourish!

Meetup offers great discoverability for many groups, but the free tier relentlessly upsells users. They can opt for Meetup+ but imagine 100 people paying $4.99/month to attend your group... and your hard work as a community organizer serves only to line the pockets of a tech giant. That is not what it looks like for your community to flourish!

It is an act of care and community stewardship to lead your group to both physical and digital places that are good for them, and many default hubs of online community organization are actively undermining the thing you seek to build! Trailwerks is only a digital stepping stone towards an in-person experience. We have no reason to keep your audience scrolling endlessly. We optimize for making it as easy as possible for your audience to RSVP and show up to an in-person event; that is where the magic happens.

Lastly, trailwerks as a platform is an investment in your brand identity.

People want community AND people want to feel like they belong to something. Belonging to a well organized and reputable outdoor recreation club is a badge of honor that is hard to match with commodity facebook groups. Trailwerks empowers clubs to own their brand and their audience.